Smoking article



3,041,21 l Patented June 26, 1962 ,041, SMOKING ARTICLE Walter Manrey Henley, Winston-Salem, N.C., as'signor to R. J. Reynolds Tobacco Company, Winston-Salem, N.C., a corporation of New Jersey No Drawing. Filed Nov. 14, 1960, Ser. No. 68,664

dClaims. (Cl. 131--17) This invention relates to a smoking article and has for an object the provision of a smoking article or composition having an improved aroma and flavor.

It is well known in the tobacco art that the domestic tobaccos which are exemplified by burley, Maryland, fluecured, bright leaf or Virginia tobaccos are low in flavor as compared with the so-called oriental or aromatic tobaccos which are imparted from Turkey, Greece, Bulgaria, Yugoslavia, Rhodesia and Russia. Accordingly, it has been common practice in the tobacco industry to prepare blends of domestic and oriental tobaccos in order to provide cigarettes Which have desired flavoring and aroma characteristics. Accordingly, it is a further object of this invention to provide a domestic tobacco which has an enhanced flavor and aroma.

A further object of this invention is the provision of a smoking article, such as a cigarette or cigar, a component part of which has been treated in order to enhance the flavor and aroma of the article when smoked.

An additional object of this invention is to provide a tobacco which has been treated in such a manner as to impart a desired cedarlik-e odor or smoothing or cooling effect which is pleasing to the smoker.

A further object of the invention is the provision of a domestic type tobacco having added thereto a chemical compound which imparts a pleasing cedarlike odor and cooling efiect to the tobacco smoke.

Further and additional objects Will appear from the following description and the appended claims.

In accordance with one embodiment of this invention, a domestic tobacco or smoking article is provided to which has been added or which has been treated with a small amount of 2,3,4a,5,6,6a,7,8,9,l0,10a,10b-dodecahydro 3,4a,7,7,la pentamethyl 7 1H naphtho[2,1-b]- pyran. The chemical structure of the above referred to compound may be represented by the following formula:

I oH-orn For convenience the compound is hereinafter referred to in this specification as compound I. It is chemically related to sclareol which latter is a compound contained in the flowering parts of Salvia sclarea. Compound I may be prepared from sclareol by the method essentially as disclosed in Ruzicka et al., Helv. Chim. Acta. 25, 621 (1942). In accordance with this method, 53.7 grams of 4 (decahydro 2 hydroxy 2,5,5,8a tetramethyl 1- naphthyl)-2-butanone [referred to in the Ruzicka et al.

article as oxyketone (11)] and 0.3 gram of platinum into 500 milliliters of Water. After neutralization of the acetic acid with K 00 the product was extracted with ether and the ether was evaporated to yield 50.8 grams of 2,3,4a,5,6,6a,7,8,9,l0,l0a,l0b dodecahydro 3,4a,7,7, 10a-pentamethyl-lI-I-naphtho[2,l-b] PYran (compound I).

Because of the presence of an asymmetric carbon atom at position 3 in the pyran nucleus of compound I, there are two diastereoisomers possible. One has a melting point of 8l82 C. While the other melts at 44-45 C. The higher melting point isomer is the predominant isomer formed in the process indicated above where platinum dioxide is the hydrogenation catalyst. If a catalyst consisting essentially of palladium on charcoal is used, the lower melting point isomer is largely produced. These isomers and other diastereoisomers of compound I and their mixtures are included as tobacco additives within the scope of this invention.

In accordance with this invention, compound I is added to tobacco or applied to a smoking article or its component parts in amounts to provide a product which contains about 0.001 to about 1.0 percent by weight of the additive. Preferably the amount of additive is between 0.02 and about 0.3 percent by weight in order to form a tobacco product having a desired flavoring and aroma. The additive may be applied to tobacco in any suitable manner and preferably in the form of a liquid solution or suspension by spraying, dipping or otherwise. The additive may be incorporated at any step in the treatment of the tobacco but is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes. Likewise it will be apparent that only a portion of the tobacco need be treated, and the thus treated tobacco may be blended with other tobaccos before the cigarettes are formed. In such case the tobacco treated may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.

In accordance with one specific example of this invention, an aged, cured and shredded burley tobacco is sprayed with a one percent ethyl alcohol solution of the above described compound I in an amount to provide a tobacco composition containing 0.07 percent by weight of the additive on a dry basis. Thereafter the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. It has been found that the cigarette when prepared as indicated has a desired and pleasing cedarlike odor which is detectable and pleasing in the main and side smoke streams when the cigarette is smoke. The smoke is also smooth and cool.

It will be particularly apparent that the manner in which the additive is applied to the tobacco is not particularly important since, as indicated, it may be done in the form of spraying or dipping, utilizing suitable suspensions or solutions of the additive. Thus Water or volatile organic solvents, such as alcohol, ether, acetone, volatile hydrocarbons and the like, may be used as the carrying medium for the additive while it is being applied to the tobacco. Also, other flavor and aroma-producing additives, such as those disclosed in United States Patents Nos. 2,766,145, 2,905,575, 2,905,576 and 2,978,365 may be incorporated into the tobacco with the additive of this invention.

While this invention is particularly useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars and other tobacco products. Also the invention has been particularly described with reference to the addition of compound I directly to tobacco. However, it will be apparent that the compound may be applied to the paper of a cigarette or the wrapper of a cigar. Also it may be incorporated into the seam paste for a cigarette. Thus a smoking article is provided which includes both compound I and tobacco although in every instance compound I need not be admixed with the tobacco as above specifically described.

It has been discovered that for certain applications, compound I has advantages over the specific cyclic ether disclosed in Giles United States Patent No. 2,905,575 as a tobacco additive. Thus compound I herein disclosed produces a very low odor at room temperature and the flavoring properties for the most part become apparent only during smoking. The odor is one that may be characterized as cedarlike. Also compound I imparts a smoothing and cooling effect to the tobacco smoke and this effect is similar to that produced by menthol but less pronounced. The fiavorant is particularly useful for incorporating into smoking articles prepared from domestic tobaccos as distinguished from the more highly aromatic oriental or Turkish tobaccos.

While particular embodiments of this invention are disclosed above, it will be understood, of course, that the invention is not to be limited thereto, since many modifications may be made, and it is contemplated, therefore, by the appended claims, to cover any such modifications as fall within the true spirit and scope of this invention.

I claim:

1. A smoking article comprising tobacco and a small amount of 2,3,4a,5,6,6a,7,8,9,10,10a,10b-dodecahydro-3,- 4a,7,7,l0a-pentamethyl 1H naphtha[2,l-b]pyran sulficient to impart a cedarlike odor to a smoker.

2. A tobacco having added thereto a small amount of 2,3,4a,5,6,6a,7,8,9,10,10a,10b-dodecahydro 3,4a,7,7,10a-

42 pentamethyl-lH-naphtho[2,1-b]pyran sufficient to impart a cedarlike odor to a smoker.

3. A domestic smoking tobacco having added thereto between about 0.001 and 1.0 percent by weight of 2,3,4a,- 5,6,6a,7,8,9,10,10a,lOb-dodecahydro 3,4a,7,7,10a-pentamethyl-lH-naphtho[2,1-b]pyran sufiicient' to impart a cedarlike odor to a smoker.

4. A process for improving domestic smoking tobacco which comprises admixing therewith a small amount of 2,3,4a,5,6,6a,7,8,9,10,l0a,10b-dodecahydro 3,4a,7,7,l0apentamethyl-lH-naphtho[2,l-b1pyran sufficient to impart a cedarlike odor to a smoker.

5. A process for improving the flavor and aroma of smoke from tobacco which comprises adding thereto in the form of a liquid suspension between about 0.001 and 1.0 percent by Weight of 2,3,4a,5,6,6a,7,8,9,10,10a,10bdodecahydro-3,4a,7,7, IOa-pentamethyl-IH naptho [2,l-b] pyran sufficient to impart a cedarlike odor to a smoker.

6. A process for improving the flavor and aroma of smoke from tobacco which comprises adding thereto in the form of a liquid solution between about 0.001 and 1.0 percent by weight of 2,3,4a,5,6,6a,7,8,9,10,10a,10b dodecahydro-3 ,4a,7,7,10a-pentamethyl-1H naptho[2,1b] pyran suflicient to impart a cedarlike odor to a smoker.

References Cited in the file of this patent UNITED STATES PATENTS 2,905,575 Giles Sept. 22, 1959 2,905,576 Schumacher Sept. 22, 1959 2,978,365 Schumacher Apr. 4, 1961 

